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North Siena Villas and Vacation Rentals

North of Siena lies the Chianti, Italy's definitive wine-growing region. This area boasts hills covered in vineyards, winding roads (favored by sporty drivers and daredevil cyclists), and breathtaking vistas.   Continue >

Displaying 61 to 90 of 63 villas
  • min $3,720/wk
  • max $5,208/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Washing Machine
  • Maid Service
" It was great..." - Barbara
  • min $8,629/wk
  • max $10,935/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
" I would and already have recommended the villa to anyone. My experience with your firm was excellent. When I return to Tuscany I intend to stay at the same locatio..." - Hal
  • min $1,680/wk
  • max $2,520/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
Displaying 61 to 90 of 63 villas

Following the old Chiantigiana road from your Chianti vacation rental you see the heart of this region, including the Chianti Classico, the Sienese Chianti, and southeast of Siena, the border of Valdarno. To the north lies San Casciano, and further north still, Florence. What to do while staying in one of our villas in Chianti? Eat, drink, and be merry. Towns like Panzano, Greve-in-Chianti, and Radda-in-Chianti---and all the wineries in between---are filled with gastronomic delights and a dizzying selection of wine shops. View our Rental Villas in North Siena..